Small-Group Chianti and San Gimignano Sunset Trip from Siena

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Small-Group Chianti and San Gimignano Sunset Trip from Siena

(65)

Add to Wishlist

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US$220.68 per guest

Adult x1

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Check Availability

Earliest available date: September 12, 2026

Free cancellation (24 hours notice)

For each guest that attends this experience, byFood will donate
10 meals

Summary

Experience Details

What You’ll Experience

Where to Meet

Reviews

Location

Siena

Duration

8 hours

Number of Guests

1 - 9 guests

Language

English

Digital Ticket

Mobile or paper ticket accepted

Experience Chianti and San Gimignano at sunset, departing from Siena. Explore vineyards, taste wines, and savor a farm-to-table dinner as you enjoy stunning views of medieval towers.

For each guest that attends this experience, byFood will donate
10 meals

Experience Details

On this afternoon and evening tour from Siena to Chianti and San Gimignano, explore the beautiful Chianti region – an area rich with dense oak forests and cypress trees – and discover its famous wine by visiting a local producer, touring their cellars and tasting their wines. Then head to the UNESCO World Heritage town of San Gimignano, famous for its medieval towers. Enjoy the main sights and browse the streets and boutique stores just as the day's crowds begin to dwindle. Visit a local farm and enjoy a farm-to-table dinner of its products and wines during sunset, in a stunning location overlooking the San Gimignano towers and the rolling, vine-covered hills.

What You Get

Traditional dinner at farm

Professional Guide

Transport by air-conditioned minivan

Gratuities

Hotel pickup and drop-off

Entrance fees to attractions in San Gimignano

Good To Know

Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
Not recommended for travelers with poor cardiovascular health
Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Suitable for all physical fitness levels
Specialized infant seats are available

What You’ll Experience

Basilica Cateriniana Di S. Domenico (Pass By)

Meet your tour guide at 2.30pm in front of the church of San Domenico in Siena and begin the tour with a comfortable drive through the Chianti countryside. Visit a Chianti wine estate, where you'll tour the grounds and wine cellars while learning about the wine-making process. Sit down and savor a tasting of Black Rooster Chianti Classico wine.

Cantinetta di Monteriggioni

After visiting a Chianti winery, visit a historic town that was once of fortress, Monteriggioni, to marvel at the medieval towers that are still intact. Monteriggioni is a perfectly preserved medieval town with a complete ring of walls and turrets, once Siena’s main bastion of defense against the armies of Florence. Today it is a quiet hamlet and you can enjoy leisure time exploring the charming streets and stores of local crafts.

30 minutesAdmission Ticket Free

Historic Centre of San Gimignano

In the late afternoon, arrive in San Gimignano as the crowds begin to dwindle and the many streets and squares of this medieval town of towers that flourished thanks to the via Francigena, an important trade route. Enjoy free time to enter its impressive church, the Collegiata di San Gimignano, or to explore the Civic Museum (entrance fees at own expense). Alternatively, shop the artisan boutiques for leather goods and hand-painted pottery; sample the fruits of the soil in the food shops and wine bars or discover the town’s many hidden beauties.

1 hourAdmission Ticket Free

Strada Statale 222 Chiantigiana

After your time in San Gimignano, head out of town to a nearby rustic farmhouse, where you'll be treated to a classic Tuscan dinner accompanied by wine. Enjoy the farm's products and wine over a convivial dinner with the others on tour that you can now call new friends.

2 hoursAdmission Ticket Included

Meeting & Pickup

Meeting Point

Piazza San Domenico, Siena Provincia di Siena Toscana, Italy, IT, 53100

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Meet under the large tree next to the red brick church

End Point

This experience ends at the meeting point.

Cancellation Policy
Cancel your booking at least 24 hours before the experience start time to receive a full refund.
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Reviews

4.8

based on 65 reviews

(TripAdvisor)

Beautiful Tuscany!

August 20, 2026

Fabulous guide (Juliana). Very personable with good information. Comfortable people carrier transport for 5 passengers and ample time at stops to see the main sites. The wine tasting with Anthon...read more

(TripAdvisor)

Nice afternoon in Tuscany.

June 25, 2026

Wonderful visits starting with interesting winery led by very enthusiastic winemaker Robert. Good and interesting wines. Nice unguided stroll about San Gimignano. Followed by nice meal at Agro Tou...read more

(Viator)

Incredible!!

December 10, 2025

This was an amazing excursion! It was worth every penny! The tour itself was so informative and fun. The food and wine were great and it’s just the right size group. Highly recommend!

(Viator)

Truly Tuscan - must not miss!

September 04, 2025

You must must must do a Tuscan adventure with these folks - our guide Keko was truly amazing - the stops, the history, the wine, the company was some of the best tours we have had - thank you Keko!

(TripAdvisor)

Truly Tuscan experience - must not miss!

September 04, 2025

You must must must do a Tuscan adventure with these folks - our guide Keko was truly amazing - the stops, the history, the wine, the company was some of the best tours we have had - thank you Keko!

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